EP2125060B1 - Procédé de charge de surfaces structurées - Google Patents
Procédé de charge de surfaces structurées Download PDFInfo
- Publication number
- EP2125060B1 EP2125060B1 EP08706775A EP08706775A EP2125060B1 EP 2125060 B1 EP2125060 B1 EP 2125060B1 EP 08706775 A EP08706775 A EP 08706775A EP 08706775 A EP08706775 A EP 08706775A EP 2125060 B1 EP2125060 B1 EP 2125060B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- poly
- paclitaxel
- balloon
- polyvinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/08—Materials for coatings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
- A61L29/16—Biologically active materials, e.g. therapeutic substances
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/416—Anti-neoplastic or anti-proliferative or anti-restenosis or anti-angiogenic agents, e.g. paclitaxel, sirolimus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2420/00—Materials or methods for coatings medical devices
- A61L2420/02—Methods for coating medical devices
Definitions
- the present invention relates to a process for the loading of structured surfaces of preferably a polymeric material with the pharmacologically active substance paclitaxel, as well as the coated medical devices obtained by this process.
- restenosis A precise conceptual description of restenosis can not be found in the literature.
- the most commonly used morphological definition of restenosis is that, following successful PTA (percutaneous transluminal angioplasty), sets restenosis as a reduction in vessel diameter to less than 50% of normal. This is an empirically determined value whose hemodynamic significance and relationship to the clinical symptoms are lacking a solid scientific basis. In practice, the clinical deterioration of a patient is often considered to be a sign of restenosis of the formerly treated vessel segment.
- Such coated catheter balloons are already off WO2005 / 089855 A1 known and the international patent application WO 2004/028582 A1 discloses wrinkle balloons which are coated in particular in the folds with a composition of a pharmacological agent and a contrast agent.
- a spray coating method for catheter balloons is known in WO 2004/006976 A1 described.
- WO 2004/028610 discloses a method of coating catheter balloons with paclitaxel, comprising: providing a catheter balloon and a solution of paclitaxel in a solvent, then coating the surface of the catheter balloon with this solution, and then finally drying the coating.
- WO 00/32238 discloses a method for coating vascular endoprostheses and balloon catheters.
- US 2006/0002973 describes a method for coating a catheter balloon with a polymeric layer into which paclitaxel is subsequently introduced.
- US 2005/0163914 describes a method for coating endoprostheses, eg stents, with active ingredients in a polymeric layer. In this case, the active ingredient is dissolved in an organic solvent and applied to the polymeric layer of the stent surface. Subsequently, the drug is precipitated by the addition of water.
- coated stents have the disadvantages described above with respect to late thrombosis, the object is to apply the drug paclitaxel on a catheter balloon that a coating is formed, which is easily detached from the balloon and can be effectively transferred to the vessel wall ,
- any commercially available catheter balloon can be used as dilatable catheter balloon.
- so-called fold balloons are preferably used, as they are for example in the international
- Such balloons have wrinkles or wings, which form largely closed cavities in the compressed state, which bulge outward during the dilatation and release substances present in the folds or can press against the vessel wall.
- Such balloons have the advantage that the substances enclosed in the folds or the paclitaxel enclosed in the folds are protected against premature detachment during insertion of the catheter.
- paclitaxel may also be incorporated or embedded in a carrier, preferably a polymeric carrier.
- a carrier preferably a polymeric carrier.
- the carrier substance is added to the solution of DMSO and paclitaxel.
- DMSO solutions containing paclitaxel and the carrier substance are then applied to the catheter balloon by conventional methods, in particular spraying or dipping methods.
- Suitable carriers are the substances which can also be used as balloon material, in particular polymeric as well as polymerizable substances, as further listed below.
- such an amount of pure drug paclitaxel may be applied to the catheter balloon that also includes a calculated amount of paclitaxel released prematurely during insertion of the catheter balloon about 30% of the total amount, nor is there a sufficiently large therapeutically effective amount of paclitaxel on the balloon when it has reached its target and which can then be transferred to the vessel wall during dilatation.
- protection of the active substance paclitaxel from premature detachment for example by introduction under the folds or by incorporation into a carrier on the surface of the catheter balloon, is preferred but not mandatory.
- the method for loading or coating of catheter balloons as well as folding balloons is usually carried out in the order of steps I) to VI) or I) to VII), wherein the steps I) and II), of course, also reversed in their order can be.
- steps IV) to VI) can also be repeated several times.
- Step V) comprising the application of a solvent capable of precipitating paclitaxel must be carried out at least once, but need not necessarily be repeated in another coating operation. Therefore, there is also the possibility that in the first coating process, steps IV) to VI), ie, the steps I) to VI) are traversed and in a repetition of the coating process, only the steps IV) to VI) or even only the steps IV) and VI) are repeated.
- the coating process is repeated once or twice or three times, but this is not mandatory. Also, a single coating operation may be sufficient to apply the required amount of paclitaxel to the catheter balloon.
- an amount of 0.5 ⁇ g to 50 ⁇ g paclitaxel per mm 2 surface of the balloon catheter to be coated and preferably an amount of 1 ⁇ g to 20 ⁇ g paclitaxel per mm 2 surface of the balloon catheter to be coated is applied to the balloon surface.
- 10 to 1000 ⁇ g of paclitaxel are applied to each catheter balloon, and 20 ⁇ g to 400 ⁇ g are preferably applied to the balloon per catheter balloon.
- Paclitaxel is commercially available from several suppliers. Paclitaxel is known under the brand name Taxol ® and still has several synonyms such as
- Paclitaxel is readily soluble in dimethylsulfoxide (DMSO), methanol and anhydrous ethanol, but it is relatively poorly soluble in water. Particularly at a pH between 3 and 5, paclitaxel is particularly stable and storable for a long time, whereas at alkaline pH it is relatively unstable.
- DMSO dimethylsulfoxide
- methanol methanol
- anhydrous ethanol methanol
- paclitaxel is particularly stable and storable for a long time, whereas at alkaline pH it is relatively unstable.
- DMSO dimethyl sulfoxide
- DSMO dissolves the required amounts of paclitaxel and only slightly attacks the material of the balloon catheter.
- the materials used for balloon catheters are those listed below, with the following polymers being particularly preferred: polyamides, polyamide-polyether-polyester block copolymers, polyurethanes, polyesters and polyolefins.
- DMSO has the property that, by successively increasing the water content, the solubility of paclitaxel in DMSO can be slowly reduced to a point where paclitaxel begins to precipitate or crystallize out.
- the structure of the precipitated paclitaxel is unclear, but it has been found that a paclitaxel coating obtained according to the method of the invention can be detached from the catheter balloon particularly well and transferred to the vessel wall.
- paclitaxel is soluble in amounts up to 150 mg / ml.
- 1 mg to 150 mg, more preferably 10 mg to 90 mg, and most preferably 40 mg to 60 mg of paclitaxel are dissolved in one ml of DMSO.
- DMSO preferably dried, i. largely anhydrous DMSO used.
- the water content of the DMSO should not exceed 5% by volume, preferably 3% by volume and especially preferably 1% by volume.
- a carrier for the active substance paclitaxel can be added to the DMSO solution.
- the carrier is preferably a biostable or biodegradable polymer, preferably selected from the group of polymers disclosed below as materials for the catheter balloon.
- the carrier substance (s) used may account for up to 70% by weight, preferably up to 50% by weight and more preferably up to 30% by weight, based on the weight of the total solution.
- the surface of the catheter balloon is structured mechanically, chemically, electronically and / or by radiation.
- the structuring of the surface of the catheter balloon has the goal to change the surface of the catheter balloon in the nanometer range up to the micrometer range, ie to create a kind of microrough surface structure.
- the surface structuring preferably takes place over the entire region of the catheter balloon to be coated and can lead to ordered structures or random structures.
- polyamides preference is given to polyamides, polyamide-polyether-polyester block copolymers, polyurethanes, polyesters and polyolefins.
- the catheter balloons are not damaged in the structuring of the balloon surface or its expansion capacity is adversely affected.
- the methods of microstructuring the balloon surface must not cause holes, micropores, or cracks in the balloon material.
- only the outer surface of the balloons is structured to a maximum depth of 1 ⁇ m.
- the structuring of the dilatable catheter balloon can be done mechanically by a grater-like device, a grater or by a blasting method with solid particles such as a sand blast method.
- a chemical-mechanical process uses a slurry or dispersion of solid particles in a solvent, especially water. Such methods are also known as chemical polishing methods. Triturating such compositions on the surface of the balloon material renders this rough without leading to deep cracks or holes.
- the structuring is carried out by means of conductors heated by current flow.
- a fine warm, hot, or glowing needle may be used to reflow the balloon material on its surface, thereby creating certain patterns on the surface, particularly as the needle moves over the surface of the catheter balloon.
- An elegant method for producing ordered structures in particular in the form of microwells or microchannels, can be achieved by the use of lasers or in principle of strongly focused radiation. These work very precisely and can be used in particular for the creation of defined structures such as gratings, spirals or lines.
- Such a surface structuring of the catheter balloon surface leads to an enlargement of the surface and thus to a possible higher drug loading in comparison to an unstructured balloon surface.
- the microstructuring thus creates a three-dimensional surface which can be loaded with a larger amount of paclitaxel. Furthermore, in comparison to the smooth untreated balloon surface, a better adhesion of the active ingredient takes place, which is also better protected by the structuring from washing off or detachment in the blood stream, since it is at least partially incorporated in the formed pores.
- the wetting of the structured or micro- to nanomodified surface of the catheter balloon can be done by all common methods.
- the solution of paclitaxel in DMSO can be applied to the balloon surface by means of, for example, spraying, dipping, plasma deposition, brushing or spraying. While most of the surface of the catheter balloon is coated in the dipping process and the plasma deposition process, spraying, brushing and spraying methods can be used to coat only a portion of the balloon surface.
- the catheter balloon it is not necessary for the catheter balloon to be completely coated.
- a partial coating or the loading of certain structural elements on the surface of the catheter balloon may be sufficient.
- a special catheter balloon with microneedles or micropores or microcompartments discloses the international patent application no. WO 02/043796 A2 Scimed Life Systems, Inc., USA, with fillable and textured areas on the balloon surface.
- the loading or filling of portions of the balloon surface would be sufficient to achieve the desired therapeutic success, of course, the entire surfaces can be coated.
- step V) of the coating method of the invention is essential where the wetted surface immediately after wetting or immediately after applying or applying the solution of paclitaxel in DMSO and before the DSMO to 50%, preferably to 25% and most preferably to 10th % evaporated, water is applied which is able to precipitate paclitaxel.
- This water is added to the DSMO and is believed to reduce the solubility of paclitaxel in DSMO.
- This water has the property that paclitaxel does not or only poorly dissolves in it, so that when adding this water to the DMSO, the solubility product of paclitaxel in DSMO is lowered.
- This water with a pH of 3 to 5 serves to precipitate the paclitaxel and is preferably distributed homogeneously in the DMSO. It is added as much precipitant preferably by spraying or spraying or pipetting, until a slight turbidity results or until paclitaxel recognizably begins to precipitate. At this point, a little more precipitation solvent can be added or the solvent mixture of DMSO and precipitation solvent is allowed to evaporate. Of course, the drying of the coating can also be accelerated by means of vacuum or vacuum, but drying on pleasure is to be preferred.
- the paclitaxel coating according to the invention which is difficult to characterize is obtained.
- Water is suitable as a precipitation solvent, since it solves paclitaxel very poor and water is also physiologically safe and harmless for the balloon material.
- water has a pH in the range of 3 to 5, and more preferably in the range of 3.5 to 4.5, on.
- the pH can be adjusted by means of organic acids and salts of these organic acids, with as few buffers as possible in the form of acids and conjugated bases should be used.
- Suitable acids for adjusting the pH are, in particular, formic acid, acetic acid, propionic acid, oxalic acid, salicylic acid, tartaric acid, fumaric acid, gluconic acid, lactic acid, malic acid, ascorbic acid, maleic acid, malonic acid, hydroxymaleic acid, pyruvic acid, phenylacetic acid, benzoic acid, glutaric acid, camphorsulfonic acid or Quinic acid (quinic acid). If necessary, it is also possible to use salts of these acids, for example sodium acetate, calcium oxalate or lithium malonate.
- the present invention relates to catheter balloons, and more particularly to pleated balloon for catheters which have been coated by a method according to the invention.
- the catheter balloons have a coating of primarily pure paclitaxel.
- the catheter balloons carry a pure drug layer of paclitaxel, which in this layer only traces of DMSO and possibly another solvent and minimal residues of the acid used and possibly their conjugated base are included.
- the paclitaxel dried on the surface of the catheter balloon has a special nature which is difficult to characterize, but seems to be essential for transfer to the cell wall and uptake into, in particular, smooth muscle cells.
- part of the paclitaxel coating is in the compressed state under the folds. This amount is sufficient to achieve the desired therapeutic result, even if the remainder of the exposed balloon surface is not coated with drug.
- the present invention also relates to catheters comprising a catheter balloon coated according to the invention.
- Such catheters are preferably used for the treatment of narrowed vessel segments, in particular of blood vessels, and for the treatment and prophylaxis of stenosis, restenosis, arteriosclerosis, atherosclerosis and fibrotic vessel narrowing.
- the catheter balloons coated according to the invention are particularly suitable for the treatment and / or prophylaxis of in-stent restenosis, ie a renewed vasoconstriction within an already implanted stent, where further stent placement within an already implanted stent is very difficult to medically not feasible.
- catheter balloons coated according to the invention are particularly suitable for treating small vessels, preferably those with a vessel diameter of less than 2.25 mm.
- catheter balloons coated according to the invention in the cardiovascular area is preferred, wherein the catheter balloons coated according to the invention are also suitable for the treatment of constrictions of biliary tract, esophagus, urinary tract, pancreas, kidney, pulmonary, trachea, small intestine and colon.
- a coated or uncoated stent i. and simultaneously with the delivery of active substance to the vessel wall during the dilatation of the catheter balloon also set a stent.
- a commercially available expandable balloon polyamide dilatation catheter is provided.
- the surface of the catheter balloon is roughened in the nanometer to micrometer range.
- paclitaxel In dried dimethyl sulfoxide (DMSO), paclitaxel (commercially available from Sigma, Fermentek, BC Biotech or Arianna International) is dissolved at a concentration of 50 mg per ml of DMSO.
- DMSO dimethyl sulfoxide
- the solution of paclitaxel in DMSO is sprayed onto the catheter balloon and then a fine mist of water of pH 3.5 is sprayed onto the surface of the catheter balloon wetted with the solution of paclitaxel in DMSO.
- the water was previously distilled and then adjusted to pH 3.5 with acetic acid and sodium acetate. The water mist is sprayed onto the wetted surface until paclitaxel begins to precipitate.
- the surface of the catheter balloon is allowed to air-dry and the coating process with paclitaxel in DMSO is repeated, followed by precipitation by water mist two more times.
- the amount of paclitaxel on the catheter balloon is 3 ⁇ g per mm 2 of balloon surface.
- the catheter balloon is dried, sterilized and the entire catheter packed.
- a pleated balloon is provided, such as in WO 2004/028582 A1 .
- WO 94/23787 A1 or WO 03/059430 A1 is described.
- the fold balloon has a total of 5 folds, which enclose a cavity in the compressed state of the balloon and bulge outwards in the expanded state, so that the balloon in the expanded state largely assumes a tubular shape.
- the fold balloon is expanded and then its surface roughened by means of a so-called "chemical polishing” method, in which method a slurry of fine particles in preferably micrometer range is used and this slurry is triturated on the surface of the expanded catheter balloon such that a roughened surface arises.
- a solution of 80 mg of paclitaxel in 1.0 ml of DMSO and 0.1 ml of methanol is prepared and stirred until all of the paclitaxel has dissolved.
- the roughened expanded catheter balloon is immersed in this solution of paclitaxel in DMSO and methanol and while the balloon is rotated with a side sprayed from water, the water previously deionized by means of ion exchange and then adjusted with as little oxalic acid and calcium oxalate to a pH of 4.0 has been.
- the catheter balloon is allowed to air dry slowly to form a fine and substantially uniform paclitaxel coating on the catheter balloon.
- the first-time coated catheter balloon is dipped an additional three times into the paclitaxel solution and then dried without again spraying it with a water mist.
- the fine paclitaxel crystals on the balloon surface serve as nuclei for the newly applied paclitaxel.
- the methanol and DMSO are allowed to evaporate and then the balloon is dried in vacuo.
- the residual content of paclitaxel in the DMSO solution can be determined so that the known initial concentration can be used to determine the amount of paclitaxel which has been applied to the catheter balloon.
- the balloon After sterilization, the balloon is provided with a protective cover which is intended to protect the active substance on the coated dilatable catheter balloon during transport and storage time and is removed by the cardiologist before insertion of the catheter.
- a commercially available expandable balloon poly-dilatation catheter is provided.
- the catheter balloon is made of a polyamide-polyether-polyester block copolymer or of polyurethane, a polyester or a polyolefin.
- Troughs or depressions or spirals or net-like patterns with a depth of 1 nm to 1 ⁇ m are burned into the balloon material by means of a laser.
- a solution of 70 mg of paclitaxel in 1.0 ml of DMSO having a water content of about 3% by volume is prepared and applied by means of a coating method or a syringe method on the horizontally lying part of the catheter balloon surface.
- demineralized water which has been adjusted to a pH of 4.8 with a mixture of tartaric acid and sodium tartrate, is applied directly to the surface of the catheter balloon wetted with the paclitaxel solution by means of a fine syringe.
- paclitaxel begins to settle. After evaporation of the solvent DMSO, the catheter balloon is rotated and another now horizontal lying portion of the balloon surface is now wetted with the paclitaxel DMSO solution and then as previously described, water is applied to this wetted surface until the paclitaxel fails. Of the Wetting and precipitation is repeated until the entire surface of the balloon is coated.
- the catheter balloon is well dried and an amorphous paclitaxel coating largely contained in the microstructures is obtained.
- the amount of paclitaxel on the catheter balloon is 2 to 4 ⁇ g per mm 2 of balloon surface.
- the balloon After sterilization, the balloon is provided with a protective cover which is intended to protect the active substance on the coated dilatable catheter balloon during transport and storage time and is removed by the cardiologist before insertion of the catheter.
- a cobalt-chromium stent coated with paclitaxel is placed on the catheter balloon of Example 1 coated according to the invention.
- the catheter balloon is coated with 3 ⁇ g solid paclitaxel per mm 2 balloon surface.
- An average patient is pretreated with about 325 mg of acetylsalicylic acid and about 300 mg of clopidogrel 12 and 2 hours before dilation.
- heparin is administered intravenously so that the coagulation time is more than 250 seconds.
- a physician-determined amount of a glycoprotein Ib / IIIa inhibitor has been administered and a guidewire is advanced to the target region.
- the catheter balloon coated according to the invention is introduced and dilated in the target region at 6 to 8 atm (about 6000 to 8000 hPa) for about 1 minute and, if necessary, deflated and another one, two or three times at about 8 atm (8000 hPa). inflated.
- Coronary angiography revealed occlusion of the RCA with collateralization of the left coronary system. Subsequently, a recanalization of the RCA was performed with an uncoated metal stent.
- ISR diffuse in-stent restenosis
- Renewed PTCA with a cutting balloon over the entire length of the RCA followed by brachytherapy in the proximal, middle, and distal regions of the RCA and PDA coronary artery was performed with the patient implanting an uncoated metal stent in the middle region of the LCX.
- Coronary angiography was again performed, showing a 70% ISR in the proximal region and a 95% ISR in the distal region of the RCA and a 60% stenosis of the PDA and PL coronary artery.
- proximal and distal lesions of RCA were treated with Cypher stent implantation.
- Coronary angiography showed complete occlusion of the RCA with collateralization from the left to the right coronary artery ( FIG. 1 , Figure A) associated with severe atheromasia of the PDA and PL coronary artery.
- Taxus 3.5x32 mm stent was implanted in the distal region of the RCA and two Taxus 4.0x32 mm stents in the mid and proximal regions of the RCA, which yielded a very good immediate angiographic result ( FIG. 1 , Picture D).
- FIG. 1 Picture D
- the patient underwent an acute myocardial infarction in 1993 and subsequently underwent primary PCI of the LAD and LCX coronary artery without stenting.
- the patient was then asymptomatic for about 14 years when he was re-hospitalized with an NSTEMI.
- the coronary angiography showed an angiographically normal left main vein and a bifurcation lesion, which caused the LAD / D1 with a 90% stenosis of the LAD, an 80% stenosis of the first diagonal ( FIG. 2 , Figure A), a 90% stenosis of the LCX in the proximal region and a 90% stenosis of a dominant RCA in the middle region.
- a temporary stenting technique was chosen for the lateral arm.
- a Quantum 3.0x20 mm (Boston Scientific) was chosen for pre-dilation at 20 atm (20265 hPa), followed by a 3.0x28 mm Xience Stent (Abbott Vascular) implantation ( FIG. 2 , Picture B). Thereafter, the diagonal side arm was dilated using a DIOR paclitaxel-eluting balloon (Eurocor GmbH, Germany) 3.0x17 at 10 atm (10133 hPa) for 2.0 minutes.
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Claims (10)
- Méthode de revêtement d'un ballonnet de cathéter dilatable comprenant les étapes suivantes:I) provisionner un ballonnet de cathéter dilatable,II) provisionner une solution de paclitaxel dans du diméthylsulfoxydeIII) exécution d'une structuration de la surface du ballonnet de cathéter dilatable,IV) mouiller la surface du ballonnet de cathéter dilatable avec la solution de paclitaxel dans le diméthylsulfoxyde,V) addition d'eau, où l'eau a un pH de 3 à 5, qui est capable précipité le paclitaxel, dans ce surface du ballonnet de cathéter dilatable, qui est humidifié avec la solution de paclitaxel dans le diméthylsulfoxyde,VI) séchant la surface du ballonnet de cathéter dilatable.
- Méthode selon la revendication 1, où le ballonnet de cathéter dilatable est revêtu dans l'état expansé.
- Méthode selon la revendication 1, où le ballonnet de cathéter dilatable pliées multiples comprenant l'étape suivante:VII) repliement des ballons pliées multiples dans l'état comprimé.
- Méthode selon une revendication précédentes, où la solution de paclitaxel dans le diméthylsulfoxyde compris 1 mg à 150 mg paclitaxel par ml de diméthylsulfoxyde.
- Méthode selon la revendication 4, où la solution de paclitaxel dans le diméthylsulfoxyde compris 40 mg à 60 mg paclitaxel par ml de diméthylsulfoxyde.
- Méthode selon une revendication précédentes, où le diméthylsulfoxyde utilisé a une teneur en eau de moins de 5 pour cent volumiques.
- Méthode selon une revendication précédentes, où au moins une substance de support est ajouté dans la solution de paclitaxel dans le diméthylsulfoxyde et cette substance est choisi parmi le groupe comprenant les substances suivantes:parylène C, parylène D, parylène N, parylène F, polyvalérolactones, poly-ε-décalactones, polyacide lactonique, acide polyglycolique, polylactides, polyglycolides, copolymères des polylactides et polyglycolides, poly-ε-caprolactone, polyhydroxy acide butyrique, polyhydroxybutyrates, polyhydroxyvalérates, polyhydroxybutyrates-co-valérates, poly(1,4-dioxane-2,3-dione), poly(1,3-dioxane-2-dione), poly-para-dioxanone, polyanhydrides, anhydrides de l'acide polymaléique, polyhydroxyméthacrylates, fibrine, polycyanoacrylates, polycaprolactone diméthylacrylates, poly-β-acide maléique, polycaprolactone butyl acrylates, polymères séquences multiples d'oligocaprolactone diols et oligodioxanone diols, polymères séquencés multiples de polyéthers PEG et poly(butylène téréphtalate), polypivotolactones, triméthyl carbonates de l'acide polyglycolique, polycaprolactone-glycolides, poly(γ-éthylglutamate), poly(DTH-imino-carbonate), poly(DTE-co-DT-carbonate), poly(bisphenol A-imino-carbonate), polyorthoesters, poly(triméthyl-carbonates), poly(imino-carbonates), poly(N-vinyle)-pyrrolidone, alcools polyvinyliques, polyesteramides, polyesters glycolés, poly(phosphoesters), polyphosphazènes, poly[p-carboxyphénoxy)propane], polyhydroxy-acide valérique, polyanhydrides, oxyde de polyéthylène-oxyde de propylène, polyuréthanes souples, polyuréthanes ayant des résidus d'acide aminé dans la chaîne principale, polyétheresters, oxyde de polyéthylène, poly(alcène oxalate) polyorthoesters ainsi que leurs copolymères, lipides, carraghénanes, fibrinogène, amidon, collagène, polymères à base de protéines, acides polyaminés, acides polyaminés synthétiques, zéine, polyhydroxyalcanoates, acide pectique, acide actique, sulfate de carboxyméthyl, albumine, acide hyaluronique, chitosane et ses dérivés, sulfates d'héparane et leurs dérivés, héparines, sulfate de chondroïtine, dextrane, β-cyclodextrines et copolymères avec PEG et polypropylène glycol, gomme arabique, guar, gelatine, collagène collagène-N-hydroxy succinimide, lipides, phospholipides, acide polyacrylique, polyacrylates, polyméthylméthacrylate, polybutylméthacrylate, polyacrylamide, polyacrylonitriles, polyamides, polyétheramides, polyéthylène amine, polyimides, polycarbonates, polycarbouréthane, cétones de polyvinyle, halogénides de polyvinyle, halogénides de polyvinylidène, éthers de polyvinyle, polyisobutylènes, aromatiques polyvinyliques, esters polyvinyliques, pyrrolidones de polyvinyle, polyoxymethylène, oxyde de polytétraméthylène, polyéthylène, polypropylène, polytétrafluoroéthylène, polyuréthanes, polyétheruréthanes, polyétheruréthanes de silicone, polyuréthanes de silicone, polycarbonate-uréthanes de silicone, élastomères de polyoléfine, polyisobutylène, gommes EPDM, fluorosilicones, chitosanes de carboxyméthyl, poly(aryléther éther cétones), poly(éther éther cétones), poly(éthylène téréphtalate), polyvalérates, cellulose de carboxyméthyl, cellulose, viscose, triacétates de viscose, nitrates de cellulose, acétates de cellulose, cellulose de hydroxyéthyle, butyrates de cellulose, acetate-butyrates de cellulose, copolymères d'éthyle-vinyle acétate, polysulfones, résines époxy, résines ABS, gommes EPDM, silicones, polysiloxanes, polydiméthyl siloxanes, halogènes de polyvinyle et copolymères, éthers de cellulose, triacétates de cellulose, chitosane et copolymères et/ ou mélanges de ceux-ci.
- Méthode selon une revendication précédentes, où les étapes IV) à VI) sont répétés plusieurs fois.
- Méthode selon une revendication précédentes, où le ballonnet de cathéter dilatable consiste d'un matériau ou un mélange de matières, où le matériau ou le mélange de matières est choisi parmi le groupe suivant de matières:parylène C, parylène D, parylène N, parylène F, polyvalérolactones, poly-ε-décalactones, polyacide lactonique, acide polyglycolique, polylactides, polyglycolides, copolymères des polylactides et polyglycolides, poly-ε-caprolactone, polyhydroxy acide butyrique, polyhydroxybutyrates, polyhydroxyvalérates, polyhydroxybutyrates-co-valérates, poly(1,4-dioxane-2,3-dione), poly(1,3-dioxane-2-dione), poly-para-dioxanone, polyanhydrides, anhydrides de l'acide polymaléique, polyhydroxyméthacrylates, fibrine, polycyanoacrylates, polycaprolactone diméthylacrylates, poly-β-acide maléique, polycaprolactone butyl acrylates, polymères séquencés multiples d'oligocaprolactone diols et oligodioxanone diols, polymères séquencés multiples de polyéthers PEG et poly(butylène téréphtalate), polypivotolactones, triméthyl carbonates de l'acide polyglycolique, polycaprolactone-glycolides, poly(γ-éthylglutamate), poly(DTH-imino-carbonate), poly(DTE-co-DT-carbonate), poly(bisphenol A-imino-carbonate), polyorthoesters, poly(triméthyl-carbonates), poly(imino-carbonates), poly(N-vinyle)-pyrrolidone, alcools polyvinyliques, polyesteramides, polyesters glycolés, poly(phosphoesters), polyphosphazènes, poly[p-carboxyphénoxy)propane], polyhydroxy-acide valérique, polyanhydrides, oxyde de polyéthylène-oxyde de propylène, polyuréthanes souples, polyuréthanes ayant des résidus d'acide aminé dans la chaîne principale, polyétheresters, oxyde de polyéthylène, poly(alcène oxalate) polyorthoesters ainsi que leurs copolymères, lipides, carraghénanes, fibrinogène, amidon, collagène, polymères à base de protéines, acides polyaminés, acides polyaminés synthétiques, zéine, polyhydroxyalcanoates, acide pectique, acide actique, sulfate de carboxyméthyl, albumine, acide hyaluronique, chitosane et ses dérivés, sulfates d'héparane et leurs dérivés, héparines, sulfate de chondroïtine, dextrane, β-cyclodextrines et copolymères avec PEG et polypropylène glycol, gomme arabique, guar, gelatine, collagène collagène-N-hydroxy succinimide, lipides, phospholipides, acide polyacrylique, polyacrylates, polyméthylméthacrylate, polybutylméthacrylate, polyacrylamide, polyacrylonitriles, polyamides, polyétheramides, polyéthylène amine, polyimides, polycarbonates, polycarbouréthane, cétones de polyvinyle, halogénides de polyvinyle, halogénides de polyvinylidène, éthers de polyvinyle, polyisobutylènes, aromatiques polyvinyliques, esters polyvinyliques, pyrrolidones de polyvinyle, polyoxymethylène, oxyde de polytétraméthylène, polyéthylène, polypropylène, polytétrafluoroéthylène, polyuréthanes, polyétheruréthanes, polyétheruréthanes de silicone, polyuréthanes de silicone, polycarbonate-uréthanes de silicone, élastomères de polyoléfine, polyisobutylène, gommes EPDM, fluorosilicones, chitosanes de carboxyméthyl, poly(aryléther éther cétones), poly(éther éther cétones), poly(éthylène téréphtalate), polyvalérates, cellulose de carboxyméthyl, cellulose, viscose, triacétates de viscose, nitrates de cellulose, acétates de cellulose, cellulose de hydroxyéthyle, butyrates de cellulose, acetate-butyrates de cellulose, copolymères d'éthyle-vinyle acétate, polysulfones, résines époxy, résines ABS, gommes EPDM, silicones, polysiloxanes, polydiméthyl siloxanes, halogènes de polyvinyle et copolymères, éthers de cellulose, triacétates de cellulose, chitosane et copolymères et/ ou mélanges de ceux-ci.
- Méthode selon une revendication précédentes, où dans la solution de paclitaxel dans le diméthylsulfoxyde, choisi parmi le groupe comprenant: abciximab, acemétacine, acétyle vismione A, aclarubine, ademéthionine, adriamycine, aescine, afromosone, akagerine, aldesleukine, amiodarone, aminoglutéthimide, amsacrine, anakinra, anastrozole, anemonine, anopterine, antimycosiques, médicament anticoagulant, apocymarine, argatrobane, aristolactame-Ali, acide aristolochique, ascomycine, asparaginase, aspirine, atorvastatine, auranofine, azathioprine, azithromycine, baccatine, bafilomycine, basiliximab, bendamustine, benzocaïne, berbérine, betuline, acide betulinique, bilobol" bisparthenolidine, bléomycine, brombrestatine, acides boswelliques et leurs dérivés, bruceanoles A, B et C, bryophylline A, busulfan, antithrombine, bivalirudine, cadhérine, camptothécine, capecitabine, acide acétique o-carbamoyl-phénoxy, carboplatine, carmustine, celecoxib, cepharanthine, cerivastatine, inhibiteur de la CETP, chlorambucil, chloroquine phospate, cicutoxine, ciprofloxacine, cisplatine, cladribine, clarithromycine, colchicine, concanymycine, coumadine, natriurétique de type C (CNP), cudraisoflavone, curcumine, cyclophosphamide, cyclosporine A, cytarabine, dacarbazine, daclizumab, dactinomycine, dapsone, daunorubicine, diclofénac, 1,11-diméthoxycanthin-6-on, docétaxel, doxorubicine, dunaimycine, épirubicine, épothilones A et B, erythromycine, estramustine, étoboside, everolimus, filgrastime, fluoroblastine, fluvastatine, fludarabine, fludarabine-5'-dihydrogènophosphate, folimycine, fluorouracil, fosfestrol, gemcitabine, ghalakinoside, ginkgol, acide ginkgolique, glykoside 1a, 4-hydroxyoxycyclophosphamide, idarubicine, ifosfamide, josamycine, lapachone, lovastatine, lomustine, melphalan, midecamycine, mitoxantrone, nimustine, pitavastatine, pravastatine, procarbazine, mitomycine, méthotrexate, cladribine, mercaptopurine, thioguanine, oxaliplatine, irinotécan, topotécan, hydroxycarbamide, miltéfosine, pentostatine, pegaspargase, exémestane, létrozole, formestane, mitoxantrone, mycophénolate mofétil, ß-lapachone, podophyllotoxine, 2-ethylhydrazide de l'acide podophyllique, molgramostime (rhuGM-CSF), peginterféron α-2b, lénograstime (r-HuG-CSF), macrogol, sélectine (cytokine antagoniste), inhibiteurs de la cytokine, inhibiteur de la COX-2, angiopeptine, anticorps monoclonales inhibitant la prolifération des cellules musculaires, bFGF-antagonistes, probucol, prostaglandine, 1,11-diméthoxycanthin-6-on, 1-hydroxy-11-méthoxycanthin-6-on, scopoletine, colchicine, NO donneurs, pentaerythrityl tetranitrate et les sydnoimines, dérivés de S-Nitroso, tamoxifène, staurosporine, ß-estradiol, α-estradiol, estriol, estrone, ethinylestradiol, medroxy-progestérone, cipionates d'estradiol, benzoates d'estradiol, tranilast, kamebakaurin et autres terpénoïdes utilisés pour le traitement anticancéreux, vérapamil, inhibiteurs de tyrosine kinase (tyrphostine), paclitaxel est ses dérivés, 6-α-hydroxy-paclitaxel, taxotères mofebutazone, lonazolac, lidocaine, ketoprofène, acide méfénamique, piroxicam, meloxicam, penicillamine, hydroxychloroquine, aurothiomalate de sodium, oxaceprol, ß-sitosterine, myrtecaine, polidocanol, nonivamide, levomenthol, ellipticine, D-24851 (Calbiochem), colcemide, cytochalasine A-E, indanocine, nocodazole, bacitracine, antagonistes du récepteur de ka vitronectine, azélastine, stimulateur de la guanidyl cyclase, inhibiteur tissulaire des protéinases métalliques 1 et 2, acides nucléiques libres, acides nucléiques incorporés dans des transmetteurs de virus, fragments de DNA et RNA, inhibiteur activateur plasminogène 1, inhibiteur activateur plasminogène 2, oligonucléotides antisens, inhibiteurs VEGF, IGF-1, substances actives provenant du groupe des antibiotiques, céfadroxil, céfazoline, céfaclor, céfoxitine, tobramycine, gentamycine, pénicillines, dicloxacilline, oxacilline, sulfonamides, metronidazol, enoxaparine, héparine, hirudine, PPACK, protamine, prourokinase, streptokinase, wafarine, urokinase ; vasodilateurs, dipyridamol, trapidil, nitroprusside, antagonistes de PDGF, triazolopyrimidine, seramine, inhibiteurs de l'ACE, captopril, cilazapril, lisinopril, enalapril, losartan, inhibiteurs de la thioprotease, prostacycline, vapiprost, interféron α, ß et γ, antagonistes de l'histamine, bloqueurs de la sérotonine, inhibiteurs d'apoptose, régulateurs de l'apoptose, halofuginone, nifédipine, tocophérol, tranilast, molsidomine, polyphénoles du thé, épicatéchine gallate, épigallocatéchine gallate, leflunomide, etanercept, sulfasalazine, étpopside, dicloxacilline, tetracycline, triamcinolone, mutamycin, procainamde, acide rétinoïque, quinidine, disopyramide, flecainide, propafénone, sotalol; stéroïdes produites en manière naturelle et synthétique, inotodiol, maquiroside A, ghalakinoside, mansonine, strebloside, hydrocortisone, bétaméthasone, déxaméthason, substances non-stéroïdiens (NSAIDS), fénoprofène, ibuprofène, indométhacine, naproxène, phenylbutazone, agents antiviraux, acyclovir, ganciclovir zidovudine; clotrimazol, flucytosine, griséofulvine, kétoconazole, miconazole, nystatine, terbinafine ; agents antiprotozoaires, chloroquine, mefloquine, quinine, terpénoïdes naturelles, hippocaesculin, barringtogenol-C21-angelate, 14-déhydro-agrostistachin, agroskerine, agrostistachine, 17-hydroxy-agrostistachine, ovatodiolides, acide 4,7-oxycycloanisomelique, baccharinoides B1, B2, B3 et B7, tubeimoside, bruceanoles C, bruceantinosides C, yadanziosides N et P, isodéoxyelephantopine, tomenphantopine A et B, coronarine A, B, C et D, acide ursolique, acide hyptatique A, iso-iridogermanal, maytenfoliol, effusantine A, excisanin A et B, longikaurin B, sculponéatin C, kamebaunin, leukamenin A et B, 13,18-déhydro-6-alpha-senecioyloxychaparrin, taxamairin A et B, regenilol, triptolide ; cymarine, hydroxy anopterine, anémonine, proto-anémonine, chloride de cheliburine, sinococuline A et B, dihydronitidine, chloride de nitidine, 12-beta-hydroxy-pregnadiène-3,20-dione, helenalin, indicin, indicin-N-oxide, lasiocarpine, inotodiol, podophyllotoxine, justicidine A et B, larréatin, malloterin, mallotochromanol, isobutyryl-mallotochromanol, maquiroside A, marchantine A, maytansine, lycoridicine, margetine, pancratistatine, liriodenine, bisparthenolidine, oxoushimsunine, periplocoside A, acide usolique, deoxy-psorospermine, psycorubine, ricine A, sanguinarine, acide Manwuweiz (Manwuweizsäure), méthylsorbifolin, sphatheliachromes, stizophylline, dihydrousambaraensin, hydroxyusambarine, strychnopentamine, strychnophylline, usambarine, usambarensine, liriodenine, daphnoretine, lariciresinol, methoxy-lariciresinol, syringaresinol, sirolimus (rapamycine), somatostatine, tacrolimus, roxithromycine, troléandomycine, simvastatine, rosuvastatine, vinblastine, vincristine, vindesine, teniposide, vinorelbine, tropfofoamide, treosulfane, tremozolomide, thiotépa, trétinoïne, spiramycine, umbelliferone, déacetyl-vismione A, vismione A et B et zéorine.
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PCT/DE2008/000095 WO2008089730A2 (fr) | 2007-01-22 | 2008-01-21 | Procédé de charge de surfaces structurées |
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US7160317B2 (en) * | 2002-01-04 | 2007-01-09 | Boston Scientific Scimed, Inc. | Multiple-wing balloon catheter to reduce damage to coated expandable medical implants |
DE20204258U1 (de) * | 2002-03-16 | 2003-07-31 | Rübben, Alexander, Dr.med., 52074 Aachen | Stent mit Beschichtung (Vitastent 2) |
DE10244847A1 (de) | 2002-09-20 | 2004-04-01 | Ulrich Prof. Dr. Speck | Medizinische Vorrichtung zur Arzneimittelabgabe |
EP1672800B1 (fr) * | 2002-12-24 | 2009-08-19 | Fujitsu Microelectronics Limited | Générateur de gigue de phase |
WO2005089855A1 (fr) | 2004-03-19 | 2005-09-29 | Abbott Laboratories | Administration de medicaments multiples a partir d'un ballonnet et d'une prothese |
DE102006055693A1 (de) * | 2006-11-23 | 2008-05-29 | Rübben, Alexander, Dr.med. | Beschichtung von Ballonkathetern zur gleichmäßigen Abgabe von Medikamenten |
-
2007
- 2007-01-22 DE DE102007003184A patent/DE102007003184A1/de not_active Withdrawn
-
2008
- 2008-01-21 BR BRPI0806821-6A patent/BRPI0806821A2/pt not_active IP Right Cessation
- 2008-01-21 US US12/524,135 patent/US20100145266A1/en not_active Abandoned
- 2008-01-21 WO PCT/DE2008/000095 patent/WO2008089730A2/fr active Application Filing
- 2008-01-21 RU RU2009131729/15A patent/RU2009131729A/ru not_active Application Discontinuation
- 2008-01-21 EP EP08706775A patent/EP2125060B1/fr not_active Not-in-force
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8597720B2 (en) | 2007-01-21 | 2013-12-03 | Hemoteq Ag | Medical product for treating stenosis of body passages and for preventing threatening restenosis |
US9192697B2 (en) | 2007-07-03 | 2015-11-24 | Hemoteq Ag | Balloon catheter for treating stenosis of body passages and for preventing threatening restenosis |
US8889211B2 (en) | 2010-09-02 | 2014-11-18 | Boston Scientific Scimed, Inc. | Coating process for drug delivery balloons using heat-induced rewrap memory |
US8669360B2 (en) | 2011-08-05 | 2014-03-11 | Boston Scientific Scimed, Inc. | Methods of converting amorphous drug substance into crystalline form |
US9056152B2 (en) | 2011-08-25 | 2015-06-16 | Boston Scientific Scimed, Inc. | Medical device with crystalline drug coating |
Also Published As
Publication number | Publication date |
---|---|
RU2009131729A (ru) | 2011-02-27 |
WO2008089730A3 (fr) | 2009-09-24 |
EP2125060A2 (fr) | 2009-12-02 |
DE102007003184A1 (de) | 2008-07-24 |
WO2008089730A2 (fr) | 2008-07-31 |
BRPI0806821A2 (pt) | 2011-09-13 |
US20100145266A1 (en) | 2010-06-10 |
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